Preparation method for 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene with high purity and high bulk density

A technology of hydroxyethoxy and bulk density, applied in ether preparation, ester reaction to prepare ether, organic chemistry, etc., can solve the problems of low yield, low purity, no reported products, etc., achieve three waste reduction, simplify post-processing steps , the effect of inhibiting the formation of by-product polymers

Active Publication Date: 2018-05-11
JIANGSU EVER GALAXY CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The resulting product 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene has a very low yield and low purity
Simultaneously these patents also do not report the fusing point of product 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene, crystal form and bulk density

Method used

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  • Preparation method for 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene with high purity and high bulk density
  • Preparation method for 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene with high purity and high bulk density
  • Preparation method for 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene with high purity and high bulk density

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In a 500 mL reaction flask, add 45.6 g (0.1 mol) of 9,9-bis(2-hydroxynaphthyl)fluorene, 200 mL of toluene, 20 g of DMAC, 1.0 g of potassium carbonate, and 22 g (0.25 mol) of ethylene carbonate. at 110-115 o C Reflux reaction for 5-6 hours, HPLC analysis 9,9-bis(2-hydroxynaphthyl)fluorene content is less than 0.1%, stop the reaction. Wash with water until neutral, separate the organic phase and cool to precipitate a solid, at 80~100 o After drying in vacuum for 12 hours, 45.8 g of 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene was obtained with a yield of 85.2% and a purity of 99.2% by high performance liquid chromatography (HPLC). , the melting endothermic peak ranges from 213-222 oC (attached figure 1 ), the weight loss on drying at 120°C is 0.10%, and the weight loss at 200°C by TGA thermal analysis is 0.2% (attached figure 2 ); Bulk density 0.45g / cubic centimeter, 1 HNMR (CD 3 SOCD 3 ) δ: 3.76(t, 4H), 4.05(t, 4H), 4.87(s, 2H, plus D 2 O disappeared), 7.01-7....

Embodiment 2

[0022]Example 2 In a 500mL reaction flask, add 45.6g (0.1mol) of 9,9-bis(2-hydroxynaphthyl)fluorene, 200mL of toluene, 20g of DMF, 1.0g of potassium carbonate and 22g (0.25mol) of ethylene carbonate . at 110-115 o C Reflux reaction for 5-6 hours, HPLC analysis 9,9-bis(2-hydroxynaphthyl)fluorene content is less than 0.1%, stop the reaction. Wash with water until neutral, separate the organic phase and cool to precipitate a solid, at 80~100 o After drying in vacuum for 12 hours, 45.8 g of 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene was obtained, with a yield of 82.7% and an analytical purity of 99.1% by high performance liquid chromatography (HPLC). , the melting endothermic peak ranges from 213-222 oC , The loss on drying at 120 degrees is 0.2%, and the bulk density is 0.48g / cubic centimeter.

Embodiment 3

[0023] Example 3 In a 500mL reaction flask, add 45.6g (0.1mol) of 9,9-bis(2-hydroxynaphthyl)fluorene, 200mL of toluene, 20g of diethylene glycol dimethyl ether, 1.0g of potassium carbonate and Ethylene carbonate 22g (0.25mol). at 110-115 o C Reflux reaction for 5-6 hours, HPLC analysis 9,9-bis(2-hydroxynaphthyl)fluorene content is less than 0.1%, stop the reaction. Wash with water until neutral, separate the organic phase and cool to precipitate a solid, at 80~100 o After drying in vacuum for 12 hours, 46.3 g of 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene was obtained, with a yield of 86.0% and a purity of 99.3% by high performance liquid chromatography (HPLC). , the melting endothermic peak ranges from 213-222 oC , The loss on drying at 120 degrees is 0.2%, and the bulk density is 0.48g / cubic centimeter.

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Abstract

The invention provides a preparation method for 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene with high purity and high bulk density. The 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene with high purity and high bulk density is prepared by condensation of 9,9-bis(2-hydroxylnaphthyl)fluorene and ethylene carbonate under an alkaline condition with polar non-protonic solvents like N,N-dimethylacetamide,N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether and polyethylene glycol dimethyl (or diethyl) ether as reaction accelerators. The 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene has a purity (HPLC) of larger than 99.0%, a bulk density of larger than 0.4g / cubic centimeter, a loss on drying of less than 0.5% (at 120 DEG C, 30 min), and a melt absorption peak at 213 to 222 DEG C. The 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene has a powder X-ray diffraction peak (XRPD) spectrum which has a morphology as shown in a figure 3 of the invention and has characteristic diffraction peaks with 2theta values of 7.7 + / - 0.20, 8.8 + / - 0.20, 12.5 + / - 0.20, 14.3 + / - 0.20, 15.5 + / - 0.20, 17.7 + / - 0.20, 18.7 + / - 0.20, 19.5 + / - 0.20, 20.4 + / - 0.20, 20.9 + / - 0.20, 21.2 + / - 0.20, 22.2 + / - 0.20, 22.7 + / - 0.20, 23.1 + / - 0.20, 24.8 + / - 0.20, 25.4 + / - 0.20, 25.9 + / - 0.20 and 26.7 + / - 0.20.

Description

technical field [0001] The invention discloses a method for preparing a photoelectric material intermediate 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene with high purity and high packing density. Background technique [0002] 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene is an important intermediate of photoelectric materials, and the epoxy resin, polyester resin, polyacrylic resin and polyimide derived from it have Excellent properties such as high refractive index, high thermal stability and good transparency have important applications in light-emitting diode packaging materials, light guide devices, light-enhancing films, polarizing films, reflective films, optical lenses, and electronic lithography materials. [0003] Japanese patents JP5513825, JP2011068624, JP2016069643 and JP2016079405 report the preparation methods of 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene, and the synthesis steps and results of these patents are the same. In this synthetic method, concentrate...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/23
CPCC07C41/16C07C43/23C07C43/202
Inventor 田礼彬陆晓峰徐卫华苏波陆国元张强
Owner JIANGSU EVER GALAXY CHEM CO LTD
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